Hydrochloric Acid → 4-Methyl-2-sulfanylbenzoic acid

HRID 539951Notes

Reaction equation

CN(C)C([S:5][C:6]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:7]=1[C:8]([O:10]C)=[O:9])=O.Cl>[OH-].[Na+]>[CH3:16][C:14]1[CH:13]=[CH:12][C:7]([C:8]([OH:10])=[O:9])=[C:6]([SH:5])[CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A round bottle flask containing a mixture of methyl 2-[(dimethylcarbamoyl)sulfanyl]-4-methylbenzoate (50 g, 197.6 mmol) and an aqueous solution of sodium hydroxide (120 mL, 4 N) was vacuumed and backfilled with nitrogen 3 times. After being refluxed for 2 hours, the resulting mixture was cooled to 0° C. and acidified with an aqueous solution of hydrochloric acid (45 mL, 6 N). The formed precipitate was collected by filtration, and then dissolved in ethyl acetate (500 mL). The solution was dried over anhydrous sodium sulfate, and concentrated in vacuo to afford 4-methyl-2-sulfanylbenzoic acid as a light yellow solid.

Workup

additionA round bottle flask containing
temperatureAfter being refluxed for 2 hours
filtrationThe formed precipitate was collected by filtration
dissolutiondissolved in ethyl acetate (500 mL)
dry with materialThe solution was dried over anhydrous sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-5870ec31c9344498bc9543a92cbe5025
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871756B2

Reaction notes

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